The bridge was funded through a $1.03 million federal grant, part of President Franklin D. Roosevelt's New Deal program, and public fundraising efforts. At first, the bridge connected Kentucky Highway 75 to Indiana Highway 75; in 1954, Kentucky 75 was redesignated U.S. Highway 431 and Indiana 75 became U.S. Highway 231.

The bridge was closed temporarily for a day and a half the weekend of March 13, 2011, due to the need for emergency repairs to the bridge deck with traffic temporarily detoured over the William H. Natcher Bridge. Following that emergency repair, transportation officials pressed ahead with planning and design on a full-depth deck rehab that was already scheduled for bidding in April 2011.

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The bridge originally was painted silver but was repainted blue sometime in the early 1970s. Over time, local residents have come to call the bridge "the Blue Bridge."

In anticipation of a repainting of the bridge initially scheduled for 2006, the local city beautification group PRIDE of Owensboro-Daviess County (Public Responsibility In Designing our Environment) sponsored an August 2003 straw poll to help determine what color to paint the bridge. PRIDE gave participants a choice of "blue," "teal," "brick red," or "green" – or participants could "write in" their own preferences.

Of the 8,245 participants in the poll, 44 percent preferred to keep the bridge its current blue. A majority of participants – 56% – preferred that the bridge be painted a different color, with 20 percent opting for teal, 18 percent for brick red, 12 percent for green, and 6 percent suggesting various "write-in" colors.[2]

Subsequently, Kentucky and Indiana highway officials indicated the bridge was scheduled for its next repainting in about 2017 (which happens to be Owensboro's bicentennial) at an estimated cost of $17 million. The repainting was rescheduled to begin in the spring of 2013.[3]

The bridge closed to traffic on May 12, 2013 for its first paint job since 1987. Originally planned to be done over the course of two construction seasons, by completely closing the span to traffic, the job was able to be fully completed (including some concrete repairs) by November 27, 2013.

Following the collapse of the I-35W bridge in Minneapolis, Minnesota in August 2007, Kentucky officials (including Governor Ernie Fletcher) sought to reassure motorists that Kentucky's bridges are safe by conducting a special safety review of all long-span bridges at that time. The Cary Bridge was subject to a detailed biennial inspection in August 2008. Kentucky and Indiana highway officials conducted a joint walk-through inspection of the structure on September 22, 2008.

On July 5, 2011, the Kentucky Transportation Cabinet closed the bridge to all traffic for a $3 million partial rehab of the bridge deck after a large hole developed in the concrete driving surface. Hall Contracting of Louisville was the prime contractor on the 3-month project. The project, which saw 40% of the bridge's deck replaced, was completed and the bridge reopened to traffic on September 30, 2011—three days prior to the October 3 deadline imposed by KYTC on the contractor.

Prior to its reopening, the bridge was opened to pedestrians and bicyclists for "Bridge Day" on Sept. 30; thousands of visitors crossed the 72-year-old span between the hours of 8:00 AM and 6:00 PM, when crews began preparing to reopen the bridge to auto traffic, which occurred at 6:30 PM.